A desirable coplanar energetic pentazolate salt driven by hydrogen bonds

A coplanar energetic salt (3) was designed and synthesized by protonation and hydrogen bonding assembly. X-ray single crystal diffraction data and theoretical calculations indicate that the incorporation of protons and robust hydrogen bonding is crucial to the planarization of the twisted molecule (1). The planarized energetic salt 3 with layer-by-layer stacking is more insensitive compared to its analogue compound 1. A coplanar and insensitive energetic pentazolate salt was effectively synthesized from a twisted molecule by protonation and hydrogen bonding assembly.